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Scientific article
English

Chiral ruthenium Lewis acid-catalyzed nitrile oxide cycloadditions

Published inTetrahedron, vol. 63, no. 35, p. 8413-8419
Publication date2007
Abstract

The synthesis of the chiral ligand (R,R)-BIPHOP-F is detailed. Its coordination to a cationic cyclopentadienyl ruthenium fragment generates [Ru (acetone)(R,R)-BIPHOP-F)Cp][SbF6], a transition metal Lewis acid that catalyzes the [3+2] dipolar cycloaddition reaction between aryl nitrile oxides and α,β-unsaturated aldehydes to give chiral 2-isoxazolines with yields of 43–98% and asymmetric purity of 60–93% ee. The stereochemistry of the major enantiomer is S, consistent with an approach of the nitrile oxide to the Cα-Si face of the enal in the anti-s-trans conformation in the catalyst site.

Citation (ISO format)
BRINKMANN, Yasmin et al. Chiral ruthenium Lewis acid-catalyzed nitrile oxide cycloadditions. In: Tetrahedron, 2007, vol. 63, n° 35, p. 8413–8419. doi: 10.1016/j.tet.2007.06.033
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ISSN of the journal0040-4020
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